反应详情

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and saturated aqueous sodium chloride, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo. Pour onto silica gel and elute with 20% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 0.31 g of the title compound; mp 94°-96° C.

1. customPartition between ethyl ether and saturated aqueous sodium chloride
2. customseparate the organic phase
3. dry with materialdry (MgSO4)
4. filtrationFilter
5. customevaporate the solvent in vacuo
6. additionPour onto silica gel
7. washelute with 20% ethyl acetate/hexane
8. customto yield a crude solid
9. customRecrystallize (hexane/ethyl acetate)